What does Luke 23:33 mean?
Jesus has reached the place of the crucifixion. Simon of Cyrene has carried the cross-piece part of the way (John 19:17; Matthew 27:32), as apparently Jesus is too weak from the beatings. A great crowd followed. Along the way, Jesus has warned a group of women that they should not weep for Him: they should mourn for themselves when judgment comes (Luke 23:26–31).Matthew and Mark identify the other two men as robbers (Matthew 27:38; Mark 15:27). We do not know what they have done. Their presence fulfills the prophecies by both Jesus and Isaiah that He would be "numbered with the transgressors" (Luke 22:36–37; Isaiah 53:12).
All four Gospels include these facts: Jesus was crucified, it was at a place called the Skull, and the criminals were to His right and left (Matthew 27:33, 38; Mark 15:22, 27; John 19:17–18). The other three Gospels include the Aramaic word "Golgotha" (Matthew 27:33; Mark 15:22; John 19:17). This was a specific hill which apparently resembled a human skull. In Greek, the term for a skull is kranion. In Latin, this was translated as Calvariae, literally "of the Skull." From this came the English name "Calvary." John 20:25–27 and Colossians 2:14 affirm that Jesus' hands are nailed to the cross beam; Luke will mention the scars in Luke 24:40.
Beyond those simple facts is a tie to Jesus' earlier teaching. James and John had approached Jesus and asked about their roles in His kingdom. They—or their mother (Matthew 20:20–21)—said, "Grant us to sit, one at your right hand and one at your left, in your glory." Jesus replied, "You do not know what you are asking. Are you able to drink the cup that I drink, or to be baptized with the baptism with which I am baptized?" They responded, "We are able." Jesus went on to say they will share His "cup" and "baptism," but He could not promise them the positions they sought: "To sit at my right hand or at my left is not mine to grant, but it is for those for whom it has been prepared" (Mark 10:35–40).
John and James were talking about thrones on either side of Jesus as advisors when He became king of the Jews. They were thinking that His "cup" was filled with glory. Now, perhaps, they are grateful others are in the places they requested. Jesus and the robbers on either side of Him are sharing the "cup" of wrath of the judgment of the Romans and the "baptism" of death. The two "advisors" give different guidance: one mocks Jesus for His apparent powerlessness; the other recognizes Him as the Christ and publicly follows Him (Luke 23:39–43).
James and John do share Jesus' "cup;" James becomes the first apostle to be martyred (Acts 12:1–2). John suffers torture, imprisonment, and exile before dying of old age.